US6503688B1ExpiredUtility
Electron beam resist
Est. expiryDec 17, 2018(expired)· nominal 20-yr term from priority
Inventors:Jon Andrew PreeceRichard Edward PalmerAlexander Phillip RobinsonToshihiko KanayamaTetsuya Tada
Y10S430/143G03F 7/038
34
PatentIndex Score
5
Cited by
11
References
19
Claims
Abstract
A high resolution patterning method of a resist layer is disclosed by patternwise irradiation of a resist layer with electron beam utilizing a polysubstituted triphenylene compound as the electron beam resist material, which is graphitized and made insoluble in both polar and non-polar organic solvents for electron doses greater than 2x10-3 C/cm2, and which undergoes cleavage of the adduct chains and extensive de-aromatization of the triphenylene core therefore enhancing the solubility in polar solvents only for electron doses between 3x10-4 and 2x10-3 C/cm2. The thus formed positive or negative tone resist layer is highly resistant against dry etching to ensure the utility of the method in fine patterning work for the manufacture of semiconductor devices.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1. A method of forming a patterned resist layer on a substrate surface comprising:
forming a coating layer containing a polysubstituted triphenylene compound on the substrate surface, the polysubstituted triphenylene compound being an electron beam resist material;
irradiating the coating layer patternwise with electron beams; and
selectively removing regions of the thus patternwise irradiated coating layer.
2. A method as claimed in claim 1 , wherein the regions of the patternwise irradiated coating layer are removed by dissolving in an organic solvent.
3. A method as claimed in claim 2 , in which the organic solvent is selected from the group consisting of chloroform, toluene and monochlorobenzene.
4. A method as claimed in claim 2 , in which the organic solvent is a polar organic solvent.
5. A method as claimed in claim 4 , wherein the polar organic solvent is selected from isopropyl alcohol, 2-pentanol, 3-pentanol and hexyl alcohol.
6. A method as claimed in claim 2 , in which the organic solvent is a non-polar organic solvent.
7. A method as claimed in claim 6 , wherein the non-polar organic solvent is a selected from aromatic hydrocarbon solvents, aliphatic halogenated hydrocarbon solvents and aromatic halogenated hydrocarbon solvents.
8. A method as claimed in claim 7 , wherein the non-polar organic solvent is monochlorobenzene.
9. A method as claimed in claim 1 , wherein the coating layer is formed by:
(i) coating the substrate surface with a solution of the polysubstituted triphenylene compound in an organic solvent; and
(ii) evaporating the organic solvent from the coating to form the coating layer containing the polysubstituted triphenylene compound.
10. A method as claimed in claim 1 in which the polysubstituted triphenylene compound is selected from the group consisting of the symmetric or asymmetric triphenylene derivatives expressed by the structural formulae:
General Formula
Example
R 1 = C n H 2n+1 , R 2 = C m H 2m+1
R 1 = C 5 H 11 , R 2 = C 2 H 5
R 1 = C 5 H 11 , R 2 = C 3 H 7
R 1 = C 5 H 11 , R 2 = C 4 H 9
R 1 = C 5 H 11 , R 2 = C 5 H 11
R 1 = C 5 H 11 , R 2 = C 6 H 13
R 1 = C 5 H 11 , R 2 = C 7 H 15
R 1 = C 5 H 11 , R 2 = C 9 H 19
R 1 = C 6 H 13 , R 2 = C 6 H 13
R 1 = C 7 H 15 , R 2 = C 3 H 7
R 1 = C 8 H 17 , R 2 = C 2 H 5
R 1 = C n H 2n+1 , R 2 = C m H 2m COOH
R 1 = C 5 H 11 , R 2 = C 5 H 10 COOH
R 1 = C n H 2n+1 , R 2 = H
R 1 = C 5 H 11 , R 2 = H
11. A method as claimed in claim 1 , in which the polysubstituted triphenylene compound is a 2,3,6,7,10,11-substituted triphenylene wherein any one or more of the alkyl groups is optionally substituted.
12. A method as claimed in claim 1 , in which the polysubstituted triphenylene compound is a 2,3,6,7,10,11-alkyloxytriphenylene wherein any one or more of the alkyl groups is optionally substituted.
13. A method as claimed in claim 1 , in which the polysubstituted triphenylene compound is 2,3,6,7,10,11-hexa(pentyloxy)triphenylene.
14. A method as claimed in claim 1 , in which the irradiation of the coating layer is conducted with an irradiation dose of between 3×10 −4 and 2×10 −3 C/cm 2 .
15. A method as claimed in claim 1 , in which the irradiation of the coating layer is conducted with an irradiation dose of at least 2×10 −3 C/cm 2 .
16. A method as claimed in claim 1 , wherein the patternwise irradiating step is conducted with a dose of electron beams such as to render the irradiated regions of the coating layer soluble in a positive tone organic solvent, and wherein the selective removal step is effected by dissolving the irradiated regions in the positive tone organic solvent.
17. A method as claimed in claim 1 , wherein the patternwise irradiating step is conducted with a dose of electron beams such as to render the irradiated regions of the coating layer insoluble in a negative tone organic solvent, and wherein the selective removal step is effected by dissolving the non-irradiated regions in the negative tone organic solvent.
18. An electron beam resist composition comprising a triphenylene derivative.
19. A method of using a polysubstituted triphenylene compound as an electron beam resist material, the method comprising: providing a polysubstituted triphenylene compound, and using the polysubstituted triphenylene compound as an electron beam resist material.Cited by (0)
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